Boceprevir

• CAT Number: I003442
• CAS Number: 394730-60-0
• Molecular Formula: C27H45N5O5
• Molecular Weight: 519.7
• Purity: ≥95%
• Target: HCV Protease
• Solubility: DMSO: ≥ 10 mg/mL
• Storage: Store at -20°C
• IC50: 14 nM (Ki)
• IUPAC Name: (1R,2S,5S)-N-(4-amino-1-cyclobutyl-3,4-dioxobutan-2-yl)-3-[(2S)-2-(tert-butylcarbamoylamino)-3,3-dimethylbutanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide
• InChI: InChI=1S/C27H45N5O5/c1-25(2,3)20(30-24(37)31-26(4,5)6)23(36)32-13-15-17(27(15,7)8)18(32)22(35)29-16(19(33)21(28)34)12-14-10-9-11-14/h14-18,20H,9-13H2,1-8H3,(H2,28,34)(H,29,35)(H2,30,31,37)/t15-,16?,17-,18-,20+/m0/s1
• InChIKey: LHHCSNFAOIFYRV-DOVBMPENSA-N
• SMILES: CC1([C@@H]2[C@H]1[C@H](N(C2)C(=O)[C@H](C(C)(C)C)NC(=O)NC(C)(C)C)C(=O)NC(CC3CCC3)C(=O)C(=O)N)C

Boceprevir (Cat.No: I003442), also known as SCH 503034, is a protease inhibitor medication used to treat chronic hepatitis C virus (HCV) infections. It works by inhibiting the NS3/4A protease enzyme that the virus needs for replication. Boceprevir is administered orally in combination with other antiviral medications, such as pegylated interferon and ribavirin. It was approved by the FDA in 2011 but is no longer commonly used due to the availability of newer and more effective HCV treatments.

Reference

1:Exploring resistance pathways for first-generation NS3/4A protease inhibitors boceprevir and telaprevir using Bayesian network learning. Cuypers L, Libin P, Schrooten Y, Theys K, Di Maio VC, Cento V, Lunar MM, Nevens F, Poljak M, Ceccherini-Silberstein F, Nowé A, Van Laethem K, Vandamme AM.Infect Genet Evol. 2017 May 9;53:15-23. doi: 10.1016/j.meegid.2017.05.007. [Epub ahead of print] PMID: 28499845 2:Factors associated with success of telaprevir- and boceprevir-based triple therapy for hepatitis C virus infection. Bichoupan K, Tandon N, Martel-Laferriere V, Patel NM, Sachs D, Ng M, Schonfeld EA, Pappas A, Crismale J, Stivala A, Khaitova V, Gardenier D, Linderman M, Olson W, Perumalswami PV, Schiano TD, Odin JA, Liu LU, Dieterich DT, Branch AD.World J Hepatol. 2017 Apr 18;9(11):551-561. doi: 10.4254/wjh.v9.i11.551. PMID: 28469811 Free PMC Article3:Efficacy and safety profile of boceprevir- or telaprevir-based triple therapy or dual peginterferon alfa-2a or alfa-2b plus ribavirin therapy in chronic hepatitis C: the real-world PegBase observational study. Mangia A, Foster GR, Berg CP, Curescu M, Ledinghen V, Habersetzer F, Manolakopoulos S, Negri E, Papatheodoridis G, Ahlers S, Castillo M, Bakalos G, Mauss S; PegBase Group Investigators..Ann Gastroenterol. 2017;30(3):327-343. doi: 10.20524/aog.2017.0136. Epub 2017 Mar 23. PMID: 28469364 Free PMC Article4:Aplastic Anemia and Severe Myelosuppression with Boceprevir or Simeprevir-Containing Hepatitis C Virus Treatment. Senín A, Broquetas T, Cañete N, Lens S, Londoño MC, Ferraro M, Forns X, Salar A, Carrión JA.Ann Hepatol. 2017 March-April;16(2):312-317. doi: 10.5604/16652681.1231593. PMID: 28233734 Free Article5:Rapid virological response of telaprevir and boceprevir in a Brazilian cohort of HCV genotype 1 patients: a multicenter longitudinal study. Borba HH, Wiens A, Steimbach LM, Tonin FS, Pedroso M, Ivantes CA, Fernandez-Llimos F, Pontarolo R.Ther Clin Risk Manag. 2017 Jan 10;13:59-64. doi: 10.2147/TCRM.S124663. eCollection 2017. PMID: 28138248 Free PMC Article6:Boceprevir — Benefit Assessment According to §35a Social Code Book V [Internet]. Institute for Quality and Efficiency in Health Care.Cologne, Germany: Institute for Quality and Efficiency in Health Care (IQWiG); 2011 Nov 29. PMID: 27905721 Free Books & Documents7:Boceprevir plus pegylated interferon/ribavirin to re-treat hepatitis C virus genotype 1 in HIV-HCV co-infected patients: final results of the Spanish BOC HIV-HCV Study. Laguno M, Von Wichmann MA, Van den Eynde E, Navarro J, Cifuentes C, Murillas J, Veloso S, Martínez-Rebollar M, Guardiola JM, Jou A, Gómez-Sirvent JL, Cervantes M, Pineda JA, López-Calvo S, Carrero A, Montes ML, Deig E, Tapiz A, Ruiz-Mesa JD, Cruceta A, de Lazzari E, Mallolas J.Int J Infect Dis. 2016 Dec;53:46-51. doi: 10.1016/j.ijid.2016.10.028. Epub 2016 Nov 1. PMID: 27815225 Free Article8:Boceprevir or telaprevir in hepatitis C virus chronic infection: The Italian real life experience. Cleo Study Group, Ascione A, Adinolfi LE, Amoroso P, Andriulli A, Armignacco O, Ascione T, Babudieri S, Barbarini G, Brogna M, Cesario F, Citro V, Claar E, Cozzolongo R, D/’Adamo G, D/’Amico E, Dattolo P, De Luca M, De Maria V, De Siena M, De Vita G, Di Giacomo A, De Marco R, De Stefano G, De Stefano G, Di Salvo S, Di Sarno R, Farella N, Felicioni L, Fimiani B, Fontanella L, Foti G, Furlan C, Giancotti F, Giolitto G, Gravina T, Guerrera B, Gulminetti R, Iacobellis A, Imparato M, Iodice A, Iovinella V, Izzi A, Liberti A, Leo P, Lettieri G, Luppino I, Marrone A, Mazzoni E, Messina V, Monarca R, Narciso V, Nosotti L, Pellicelli AM, Perrella A, Piai G, Picardi A, Pierri P, Pietromatera G, Resta F, Rinaldi L, Romano M, Rossini A, Russello M, Russo G, Sacco R, Sangiovanni V, Schiano A, Sciambra A, Scifo G, Simeone F, Sullo A, Tarquini P, Tundo P, Vallone A.World J Hepatol. 2016 Aug 8;8(22):949-56. doi: 10.4254/wjh.v8.i22.949. PMID: 27574549 Free PMC Article9:Efficacy and safety of boceprevir-based triple therapy in HCV cirrhotic patients awaiting liver transplantation (ANRS HC29 BOCEPRETRANSPLANT). Fontaine H, Maynard M, Bouix C, Carrieri MP, Botta-Fridlund D, D/’Alteroche L, Conti F, Pageaux GP, Leroy V, Métivier S, Anty R, Durand F, Canva V, Vilotitch A, Lebray P, Alric L, Duvoux C, Petrov-Sanchez V, Beaulieux F, Wellems C, Paul C, Roque-Afonso AM, Roche B, Pradat P, Samuel D, Duclos-Vallée JC; BOCEPRETRANSPLANT study group..Clin Res Hepatol Gastroenterol. 2017 Feb;41(1):56-65. doi: 10.1016/j.clinre.2016.06.006. Epub 2016 Aug 20. PMID: 27554134 10:[Efficacy and safety of boceprevir based triple therapy in Hungarian patients with hepatitis C genotype 1 infection, advanced stage fibrosis and prior treatment failure]. Hunyady B, Abonyi M, Csefkó K, Gervain J, Haragh A, Horváth G, Jancsik V, Makkai E, Müller Z, Ribiczey P, Sipos B, Szabó O, Szalay F, Szentgyörgyi L, Tornai I, Újhelyi E, Varga M, Weisz G, Makara M.Orv Hetil. 2016 Aug;157(34):1366-74. doi: 10.1556/650.2016.30538. Hungarian. PMID: 27546804